Figuring things out, five suits and two bottles of wine at a time

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At the Airport

The glory days and romance of airports and train stations are long gone. Today, travel is about long lines, crying children, mediocre food and the occasional inglorious sprint to one’s gate. Still, we persevere and try to look good doing it. Really it comes down to this: Versatility and Comfort.

Today’s post is about the first portion of the trip, the airport or train station. The latter is much less of a hassle, but either way, the rules are this: comfortable shoes, dark clothes, a good blazer, and a good bag.

Shoes. No monkstraps. Yes, they look great but they are a hassle to take on and off. Surviving the airport is about efficiency and monkstraps are anything but. If traveling for work and it is a short trip, then I usually only bring one pair of shoes and they are nearly always black dress shoes as the suits I will be wearing for meetings are nearly always dark.

Fun tip: Switch out the laces to something colorful while traveling and switch back to dark laces for the work meetings.

Dark Clothes. Travel in darks. Three reasons: They are easy to match and it isn’t the end of the world if you spill something on yourself. Plus, it’s tough not to look good in black. I like a good pair of dark jeans or chinos–they are comfortable, they don’t wrinkle easily, and I can wear them with most anything. I match that either with a button-down shirt or a polo.

The pocket square and laces add the pop to an otherwise conservative outfit

The Blazer/Sweater. I love wearing blazers while traveling as it classes everything up and you can use a brightly-colored pocket square to show some personality. However, once you are on the plane, unless you are in first class, there is the question of what to do with the blazer–fold it and hold on to it? Wear it and wrinkle it up? Fold it and stuff it into the overhead? If it’s too much of a hassle, there is the simple and clean v-neck sweater as an alternative.

The Bag. For trips under three days, I tend to go with the mantra of “What Would James Bond Do?” and let me tell you something: He wouldn’t own a rolling suitcase. A weekender bag looks good, it’s distinctive, it easily fits in the overhead, and it forces you to pack light. Finally, it’s a god damn conversation piece. Look at that bag. It’s gorgeous.